


Confessions of a Cam Boy

by MsCaptainWinchester (rons_pigwidgeon)



Series: Confessions of a Cam Boy and Timestamps [1]
Category: Supernatural
Genre: Age Difference, Alternate Universe - Office, Anal Fingering, Anal Play, Anal Sex, Blow Jobs, Boss/Employee Relationship, Bottom Dean, Camboy Dean, College Student Dean, Coming Untouched, Daddy Kink, Dean has a Panty Kink, Food Kink, Food Sex, Internet, Interns & Internships, John Winchester's A+ Parenting, Light Dom/sub, M/M, Masturbation, Mentions of homophobia, Nipple Play, Office Sex, Panty Kink, Rimming, Sandover, Sandover Bridge & Iron Inc., Semi-Public Sex, Sex Toys, Top Castiel, Voyeur Benny, Voyeur Castiel, Voyeur Lucifer, Voyeurism
Language: English
Status: Completed
Published: 2016-11-26
Updated: 2016-11-26
Packaged: 2018-09-02 06:36:00
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 13,020
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8654578
Author URL: https://archiveofourown.org/users/rons_pigwidgeon/pseuds/MsCaptainWinchester
Summary: Dean runs a cam show to pay his way through marketing school, but he's about to start an internship that he doesn't know will change his life. Watching Dean's show is Castiel's favorite way to wind down after a stressful day at Sandover Bridge & Iron. When Cas comes to work one day and finds his favorite cam boy setting coffee on his desk, he is completely thrown. Will Dean finish his internship without knowing his favorite viewer is his new boss, or will he be able to see through Cas' non-existent poker face and figure it out?





	

**Author's Note:**

> This was written for the Dean/Cas Big Bang challenge. Thank you to my glorious beta and favorite person in the world, Tacky Goldring, for helping me be the best writer I can be.

Dean takes a final look around his room, checking the lighting, making sure his bedspread is smooth and that he remembered to take down his pictures of Sammy and his parents. Once satisfied, he settles onto the edge of the bed, ready to get started. He’s buzzing with anticipation, excited to see what this night will bring. It’s been almost a week since his last show, and he doesn’t like to keep his viewers waiting. He makes sure to send out a tweet and the Instagram pic he had set up as a reminder to his followers that he’s about to go live before logging into the site and opening his stream.

It only takes a few seconds for the watcher count to climb into the hundreds. He grins, waving at the camera. “Hey guys, it’s been a while. Did you miss me?” He gets a flurry of messages, some happy, most lewd. One guy tells him to take his cock out, which he chooses to ignore. It wouldn’t be a good show if he revealed everything at once.

“I know, I missed you guys, too, but finals week, you know?” He shrugs, still smiling at the blinking light above his laptop screen, reaching next to him for the dildo he’d left on his night stand, just out of view of the camera. “I got a new toy to play with tonight, to make up for being gone. It’s a big one. Think it’ll fit?” It’s purple with thick ridges lining the shaft and a strong suction cup at the base so Dean can mount it on a chair and ride it if he wants. He wraps his pointer finger and thumb around the widest part of the shaft to show how thick it is, his fingers only barely overlapping. It’s the widest dildo he’s ever tried, and if he wasn’t so sure it was going to get him a large up-tick in paid viewers and probably a couple more one-on-one sessions than usual, he might be nervous.

He flops the dildo up and down a few times to show how stiff it is, hamming it up for the camera. He gets a flurry of replies, too many to read at once, but they all look excited. He sets the dildo down with a last wiggle. “We’ll play with that more later. I think right now, I’m probably wearing a few too many clothes, don’t you?”

His answer comes in messages speeding down his chat box. He bites his lip as he reaches for the hem of his shirt, pulling it up high enough to reveal a few inches of his taut abs before dropping it back down again and laughing at the several dozen protests that appear. He picks it back up again and slowly peels it off. He holds it out towards the edge of the bed and drops it, staring at the camera with a smirk. There are more messages, and he takes time to read them as he rubs his hands over his chest, tracing the bare skin over his heart and snagging a nipple between his thumb and forefinger, plucking at it until it’s hard. He bites his lip again, enjoying the twinge of pain when he pinches just a little too hard.

There are a lot of requests, but the user that catches his eye is his favorite, his most frequent one-on-one viewer, **iwatchthebees75**. Bee-man, as Dean started to refer to him when their one-on-one sessions became more frequent, is the person responsible for the new dildo, though Dean doubts he knows it. He had paid for six private shows in the last month, and the extra income had gotten him enough ahead to justify splurging on the dildo. It didn’t hurt that the man—Dean has always assumed he is a man, though he has no way of knowing--knew how to give a good order. It made Dean’s nerves sing every time he followed through. Dean leans closer to the camera. “Hey Bee-man, glad to see you here. Did you see the new dildo?”

He gets an affirmative and gives the camera a thumbs-up. He spots two more of his favorite regulars joining the room one after another, **cajunboy1872** and **morningstar666**. They greet each other before Dean has a chance, and he smiles at the bickering that ensues. The two pretend to be bitter rivals for Dean’s attention, but he secretly thinks they’d fuck if they ever met up. He loves their banter. “I see the insults have started early, CB, Morningstar.” He sends them a wink that gets them bickering over who it was for and laughs.

After reading through the chat for a few more seconds, he decides he’s spent enough time idle. He starts running his fingers up and down his torso, just grazing the skin around his areola before sliding back down, teasing them.

 **Pinch your nipple and tug until it hurts,** Bee-man tells him. He tugs at the nipple and the sensation of the pain is enough to pull the first moan of the evening from his lips. He rubs his fingers around the areola, soothing the skin there before dragging his hand further down his body to the edge of his jeans. He’s starting to sweat a little under the stage light he has set up, a fine sheen of moisture dotting his skin. He moans again, teasing at the button of his jeans while he moves his other hand over his clothed crotch, stroking himself through his clothes. He’s already working on an erection, the thrill of being watched by hundreds of guys always enough to get him excited. He bucks his hips into his hand, moaning as he leans back on one elbow.

He tries to keep an eye on the chat window, pleased to see that the number of viewers has reached 2,037. He plucks at the button closer to his jeans a couple times, still teasing. More of them pay later on when he takes his time during the free pre-show, so he does, pulling the zipper down agonizingly slowly. When he has the jeans open, he slinks off the bed to stand in front of the camera, turning to show them his backside as he slowly bends over, lowing the jeans as he goes. He wiggles his hips to the beat of the music he has playing in the background, grinning over his shoulder at the camera. All the appreciative comments only serve to boost his ego enough to drop the jeans entirely and step out of them.

He has the black lace panties on tonight, and the scratch of the cheap lace feels good against his skin. He had never thought to try women’s underwear before starting the cam show, but Bee-man requested them, and Dean had quickly become addicted to the feeling. He stays leaning over the bed as he snags at the elastic of the panties, wiggling more.

He turns around, running a hand over the erection barely concealed by the black lace. “I’m already hard, you guys. It’s been too fucking long since our last show. All of you watching me is too much,” he tells them with a bite of his bottom lip as he lays back on the bed again. He lifts a foot to the edge of the bed to give them a better look at his cock and the tease of his pucker barely hidden behind the sheer lace. He traces his fingers over the edge of the panties, pulling them aside enough to give them a real peek and grinning at the response that gets.

“You want me to take them off, do you? Getting a little ahead of yourselves, aren’t you? We’ve got all night.”

He is quickly informed by no less than seven viewers how long it’s been since his last show, and he has to laugh at their enthusiasm. “If you’ve waited five days, what’s another few minutes, baby?” He laughs harder at the response that gets him. “Alright, alright. Impatient,” he teases as he rolls onto his hands and knees on the edge of the bed, widening his legs as far as he comfortably can to give them a good view of his spread cheeks. The lace is stretched enough to show them at least a peak of his pucker. He runs his hand down his lower back until it snags on the lace and starts to pull them down. They settle over his hips, exposing his bare ass to the camera. He rubs his fingers over his exposed entrance, humming at the pleasure the touch brings him. He hasn’t even had much time to masturbate lately with all the studying he had to do for finals. It feels amazing to be able to touch himself again.

He checks the chat through his spread legs and finds a request to spread his cheeks wider to give them a better look. He drops onto his shoulder to reach behind himself, spreading his cheeks and gently fingering his tight, dry hole, opening it for them. He knows it’s going to be gaping by the time he’s finished tonight. He plays with himself a little more before reaching for the lube. It’s awkward to finger himself on his hands and knees, but it gives the viewers a better view of what he’s doing, so he spends a few minutes shallowly fingering himself that way. His reach is limited, though, and he eventually becomes as impatient as they are. He pulls his fingers out and wipes them on the towel on the edge of the bed before turning and sitting next to the towel to catch up on the chat.

 **Fuckurface324** wants him to get to the dildo already, but he isn’t a paying viewer, so Dean just tsks at him. “Sorry, 324, but I’m saving that for my premium show. You can subscribe to my channel or do a one-time sign-up if you really want to see how good it stretches my hole.” He picks up the dildo again and licks a line up the shaft, winking at the camera. “I’m thinking you might.” He knows 324 won’t. That guy never pays and always bitches about how little Dean does for his free viewers. Dean doesn’t pay the guy any more attention.

 **Iwatchthebees75** tells him to suck on his fingers and rub them up his perineum. He shoves the panties all the way off his legs and leans back on an elbow with a leg on the bed again, sucking on his fingers in the dirtiest way he can manage. When they’re good and wet, he reaches behind his balls and rubs them up and down the space behind, moaning at the pleasure that takes over his body.

“Oh fuck, that feels good,” he gasps, reaching lower to finger himself again, deeper this time. He pushes his hips into his hand, forcing the fingers as deep as they can go, moaning as he just manages to brush his prostate. It doesn’t take him long to start leaking pre-cum onto his stomach, a wet line trailing up the dark blond of his happy trail.

He glances at the computer, checking the time. He’s been streaming for half an hour, long enough for free users. He sits up, wiping his fingers off again. “As much fun as this is, I’m ready for a little more, aren’t you?”

He gets a flurry of affirmatives and grins at them all. “Okay, I’m going to switch to a premium room, then. Thank you to all my non-premium members for stopping in. I’ll check back at the end of the show. And remember, if you aren’t already a subscriber, you can join the party any time you like.” He picks up the dildo again and waves it at the screen in farewell to his free users, hoping it’s enticement enough for at least a few of them to decide to go pay. He takes a few seconds to switch the room to a premium level and half the users drop off.

He smiles at his premium users and holds the dildo higher. “Now that we’re alone, shall we get started?” There are a few dozen eager messages. He grins, turning his attention to the dildo, the translucent material shining in the light. “How long do you think it will take me to take all of this?” he asks.

He reads the responses, laughing at a few of the lewder ones. “You all really want this in my ass, don’t you? Luckily, so do I. Let’s do this.”

He adjusts the platform he has his laptop set up on until it shows he bed at a higher angle and then lays back against the soft jersey sheets, pulling both his knees up to his chest to completely expose his hole. He sucks on the head of the dildo a few times to get it wet before reaching for the lube. He takes his time coating the shaft, stroking up and down in slow, sensual motions to entice his audience. When he has it nice and wet, he reaches down and teases it against his entrance, tiny sparks of pleasure shooting up his spine with each brush.

It doesn’t take him long to grow impatient with the teasing and press the dildo inside, but it’s wider than he’s used to and doesn’t go in easily. He whines at the slight pain and pulls it out to try again, squeezing a good dollop of lube over the tip and his asshole. The second attempt goes better, and Dean finds himself knocking his head back with a moan. “Oh fuck yeah,” he groans, shifting his hips down to press more of the shaft inside.

It takes a little bit of work to get more than an inch past the head, but he is soon sliding the dildo in and out easily, moaning loud enough that his neighbors can probably hear him through the thin walls as he fucks himself. He starts to stroke his cock to the rhythm of the dildo fucking into him, losing himself a little in how good it all feels. He rolls his head to the side to check the chat and sits up a little. “You want to see me cum without touching myself?” he asks, seeing the request from Bee-man and a dozen messages after echoing this desire. He licks his lips, shifting his hips down, using the bed as leverage to push the dildo in further. He feels stretched wide with it, fuller than he’s ever felt with a dildo, though he did fuck a biker dude once who was bigger. That had been heaven.

He lays back against the bed and rocks his hips onto the dildo again, aiming for his prostate. He closes his eyes and thinks about the biker. Dean had felt dwarfed by him, and the heavy weight of him over Dean had been so sexy. He pushes the dildo in harder, imagining it as Zeke, holding him down and fucking him until he sees stars. He cries out, hitting his prostate one final time before his orgasm rushes over him, knocking him back as cum splatters over his chest and stomach.

A few drops hit his chin, and he can’t help but chuckle as he sits up to show them. He’s panting, probably flushed red with exertion. He thumbs at the drops on his chin and pops his thumb into his mouth, licking the salty cum off with a mischievous smile at the camera. “That was a good one. Thanks for the suggestion, Bee-man.”

He opens the room up to free users again, wiping the cum off his chest with slow strokes of his fingers and licking it off as he chats with them all for a little while longer. He eventually has to sign off, telling them he has a big day in the morning, but not that the big day is the start of his marketing internship. He closes out of the room and spends a few minutes checking his account to see how much money he made. $650 for a little over an hour. Not bad.

He grins to himself as he logs out and starts to clean up, happy that it went well and full of adrenaline from the rush of having so many strangers watching him do something so dirty. By the time he has his equipment put away and the room set back to its usual state, it’s later than he would like. He takes a shower and crawls into bed with a grin on his face.

/

Dean checks his tie in the reflection of the brushed metal plating one last time before the elevator doors open and he steps out onto the fifteenth floor of Sandover Bridge & Iron Inc. He makes sure he has his cell on silent as he steps up to the reception desk and smiles at the pretty brunette woman sitting there. “Hi, my name is Dean Winchester. I’m supposed to be starting an internship with Mr. Novak today,” he tells her.

She gives him an appreciative once-over before smiling at him and holding her hand out. “Good morning, Dean, welcome to Sandover. Mr. Novak isn’t in yet, but let me show you where your desk will be and get you settled.”

Dean shakes her hand and follows her through a winding set of cubicles to a closed office door. She tells him her name is Meg as they walk, and that she is acting as Mr. Novak’s secretary while the other woman is out on maternity leave. She opens the office door to reveal a plain room and an interior door that must lead to Mr. Novak’s office. “Here’s your desk.” She turns and looks him over as if considering something. “Okay, so I know I said I’m doing the secretarial stuff, but I only mean I’m doing his scheduling and taking his calls. Since you’re using Hannah’s desk while she’s gone, you’re in charge of Castiel’s personal needs.” Dean wants to ask what that means, but she keeps talking. “It’s good that you came early. Castiel likes to have his coffee set out for him when he gets in, and as the person who will have to deal with him should he not get that coffee, I am going to advise you to make sure it’s on his desk before 7:00.”

Dean raises an eyebrow. Is this guy an asshole? Dean worked hard to get this internship, and the last thing he wants to have to deal with now that he’s gotten it is a difficult boss who won’t teach him anything. His expression must show his thoughts because Meg smirks at him. “Cas is the best boss you’ll ever have when he’s caffeinated, but he is a total asshole in the morning before he’s had any. Make sure it’s ready and don’t make eye contact until he’s drunk at least half of it, and you’ll be fine.” She pats his shoulder and turns and leaves before he can ask her where the coffee maker is.

He opens and closes his mouth a few times, listening to her high heels clicking down the hallway through the open doorway. After a moment, he collects himself and drops his messenger bag behind the desk he guesses is his. He peeks into the inner office to see if there’s at least a cup he can use and is surprised to find a large space with a wall of windows at the back. There’s a fancy modern-looking desk in the center of the room that looks like it cost a lot of money, but also like it might fall apart at the slightest touch. Inlaid in one of the walls is a mini coffee bar with one of those fancy coffee makers that grinds the beans and brews the coffee all at once.

Dean lets out a breath upon seeing the coffee maker and goes over. There’s a line of coffee cups arranged on a shelf underneath it. He picks a black one with bees painted on it, smiling at the reminder of his favorite cam watcher, and puts it onto the drip tray. After that, he’s a little lost.

He takes a minute to look the machine over. He’s never used one of these before. His own drip coffee maker at home is easy to use. Pour water, put filter and grounds in basket, turn on. This thing looks… complicated. He pulls his phone out to check the time. It’s not even 6:30 yet. He’s got time. He googles the machine and takes a few minutes watching a YouTube video to see how it works. It is complicated, but Dean can handle it.

He is just setting a fresh cup onto the desk next to the computer monitor when the office door opens and a gorgeous man walks in. He’s wearing a dark blue suit and a bright blue tie, both matching his large, bright blue eyes. Eyes that are fixed on Dean with a stunned expression, the man frozen in place with his hand still on the doorknob.

Dean straightens and manages a smile, unsure what to do. Meg had told him not to make eye contact until after Mr. Novak had had his coffee, but he's already fucked that up. He decides to just go for it and hope he doesn't get his head chewed off. "Hey, sorry to invade your space, but Meg told me you liked to have your coffee as soon as you get in?" When the man continues to stare at him, Dean continues, stepping around the desk to approach him with a hand up to shake. "I'm your new intern, Dean Winchester."

Mr. Novak lets go of the door handle to shake his hand, still dazed-looking. "Castiel Novak," he says, and his voice is much deeper than Dean would have expected. It rolls down Dean's spine and sets his nerves tingling.

"Is there anything I can do for you while you're getting started this morning?"

"No—" He clears his throat as though gathering himself. "Thank you, but no. Please ask Meg to direct you to HR to get your email and computer login information set up. I will be ready to go over your duties when you get back." The confusion is gone from his expression, replaced with a confident instructive tone that plays right into Dean's need to please.

"Of course, sir. I'll be back as soon as I can." Dean steps around him and opens the door, glancing over his shoulder just long enough to see Castiel approach his desk and drop his briefcase onto it. Dean quiets the voice in his head that tells him the back looks as good as the front and does as instructed.

When he gets to the reception desk, Meg raises an eyebrow at him. "Did he fire you already?"

Dean shakes his head. "He was fine? He uh, wants me to go to HR and get me email and login?"

Meg stares at him for a few seconds. "He was fine? He literally growled at me when I said good morning to him."

"I don't know what to tell you. He looked like he forgot I was going to be here, but otherwise, yeah. Fine. Can you tell me where HR is?"

She looks like maybe she still doesn't believe him, but tells him what he needs to know.

/

A week spent in Mr. Novak's presence, and Dean can already tell he is going to have a problem. Mr. Novak is the kind of sexy that makes it hard for Dean to think. Meg had been right about him being a great boss. He gives clear instructions and helps Dean learn to navigate the Sandover filing system with infinite patience. The problem is his voice. He leans over Dean's chair to point something out to him and explains what Dean needs to do right in his ear, and it's like warm oil dripping down his spine every time.

Dean resists the temptation to flirt with his boss, but each day is a hard-won battle. Novak himself isn't helping. He looks at Dean sometimes like he wants to peel his clothes off layer by layer and lay him out like a buffet. Dean has been the recipient of similar looks for half his life, but no one has affected him the way Novak does. The worst part is that it’s clear by his body language that Novak is trying as hard as Dean to keep things professional. Every time he gives Dean one of those looks, as soon as he catches himself he shakes his head and frowns at himself. He usually ends up skulking back to his office and hiding for a few hours afterwards.

Dean works hard to keep his head down, focus on the work. Novak has him working on a marketing campaign for a new high rise in Columbus, and it is teaching him a lot about how to work with graphic designers and how to create functional strategic marketing plans. He is in the middle of scheduling the roll-out of a line of public transit advertisements promoting the low cost of living for the new high-rise when Novak emerges from his office for the first time that morning.

“I have a lunch meeting with a client to discuss a large-scale remodeling project. Would you like to accompany me?” Novak asks, approaching the desk.

Dean is surprised by the offer, but stands up immediately and reaches for his jacket. “Are you sure?” he asks.

“Of course, I wouldn’t have invited you if I wasn’t. It will be a good learning experience for you to see how these sorts of lunches tend to go.”

“That would be awesome. Thank you,” he says, pulling his jacket on. He doesn’t miss the way Novak’s eyes slide down his body as he moves. When his eyes meet Dean’s again, they’re wide with realization that he’s just been caught. Dean smiles at him, resisting the urge to wink. Novak clears his throat and directs Dean towards the door.

“Shall we?”

They take a company car, a new experience for Dean. It’s a Cadillac with a wide back seat that Dean and Novak share. There’s a driver, but Novak didn’t introduce them. “We are meeting Fergus MacLeod today. He owns a chain of nightclubs and restaurants that he is looking to remodel extensively. This is our first meeting on this project, and he has been close-lipped about what he is looking to do, so I do not know what to expect from him. Regardless, you will not be expected to contribute. I would just like you to take notes on the meeting. Do you think you can do that?”

Dean nods, holding up the tablet he made sure to take with him. “I can do that, sir.”

“Good.” Novak smiles at him, but hesitates before speaking again. “I should warn you that Crowley can be a bit... trying to deal with. He has very exacting taste and does not like to hear the word no. He also enjoys flirting with anything that stands still long enough, especially interns. Ignore him and you will be fine.”

Dean nods, opening up a document on the tablet to set his notes up before they get to the restaurant. "I can handle flirting, sir."

"I'm certain you can. It's probably something you deal with all the time." Dean whips his head up at the tone, but Novak already look s like he regrets his words. He turns his attention out the window, a light pink appearing on his cheeks. Dean hides his smile and turns away, too. He pushes down the fluttery feeling in his stomach, hardening himself. He cannot be attracted to his boss, no matter how much he wants to be. It isn't professional, and he is not about to ruin a hard-won internship because of the whims of his dick. He can save whatever fantasy pops into his mind for his cam shows and forget the rest.

The awkward tension between them persists up until the moment MacLeod approaches their table and sits down, eyeing Dean up and down like a piece of meat, just like Novak had warned Dean. "Castiel, you didn't tell me you would be bringing me such a tasty morsel to feast my eyes on during our meeting. You're stacking the deck against me." He turns shrewd eyes to Mr. Novak. "It isn't going to distract me, you know."

Dean fights the urge to roll his eyes. "Crowley, this is Dean Winchester, the firm's newest intern. He is shadowing me for the next few months, and I thought this meeting would be a good opportunity for him to learn and take notes. Please refrain from sexually harassing him."

"You are no fun." MacLeod sneers at Novak, but it doesn't have any bite to it. The rest of the lunch is fine, minus a few appreciative looks and a hand on his knee at one point. Dean keeps his head down and takes notes diligently, not about to fuck up Novak's deal because of a stray hand.

When they get back in the car, Novak turns to him. "Did my imagination get away with me or did put a hand on your knee?"

Dean fiddles with the tablet, making sure his notes got saved. "He uh... he did, yeah. No big deal."

Novak furrows his brow and his entire demeanor hardens, becomes... fierce. He reminds Dean of a warrior preparing for battle, the complete opposite of the serious, sort of goofy guy Dean had seen so far. Dean can't help but find it incredibly sexy. "If Crowley or anyone else touches you without your permission again, I want you to say something immediately. I don't care how important you think the client is or how minor you view the infraction. Sexual harassment is sexual harassment, and I will not sit back and let it happen. You are worth more than to be on the receiving end of it. Do you understand me?"

Dean nods, eyes fixed on Novak's sharp blue gaze, unable to look away. "Okay."

"Good. This applies to your own professional career as well. You deserve to be treated with respect and dignity, and not like an object to be toyed with. Never let anyone attempt to take advantage of you or manipulate you, even if it appears that such treatment will benefit your career. You are an intelligent, motivated young man, and you will do great things all on your own merit."

He's heard it before, but he wonders if Novak would say the same if he knew what Dean did to support himself and pay for school. Would he be so willing to tout Dean's self-worth if he knew that Dean spent his nights jacking it for dudes on camera? Dean forces a smile and looks away, not saying anything. He can feel Novak's eyes on him for the rest of the ride back to the office, but thankfully no more words are exchanged.

/

By the fifth week of his internship, Dean has grown to understand the rhythm of Mr. Novak's moods and started to get his dry, deadpan humor. He is still overwhelmingly attracted to the guy, but he also likes him as a person, and it is this point that is making it hard for Dean to resist flirting. Novak has started treating Dean to lunch when he isn't meeting clients, ordering in meals for them that they eat together in Novak's office. It is maybe a little more intimate than a professional relationship should be, but it is the reason Dean knows that Novak has two brothers and volunteers at an apiary in his spare time—Dean hadn't even known what an apiary was until Novak explained it to him. Dean finds it funny, and maybe a little comforting to know Novak shares Bee-man’s interest, but he doesn’t think it’s anything but a coincidence until that Monday.

"Did you enjoy your weekend with your brother?" Novak asks as they share fried rice.

Dean frowns as he chews his bite of egg roll, racking his brain for a time he had told Novak that Sammy was coming to visit. He had been careful not to talk about his family, trying to keep at least a little bit of distance between his personal life and his boss.

And then it hits him. The cam show. He hadn't mentioned anything about Sammy to Novak, but he had told his subscribers that he wouldn't be streaming last weekend because his brother was coming to stay with him. He stares at his boss for a long moment, unable to compute what his brain is telling him must be the truth. Novak _knows._ Novak _watches his show_.

Dean puts the egg roll down and clears his throat. "It was uh... it was good. I don't get to see him much since moving here for school." He doesn't mention that getting Sammy to Ohio had been a struggle of will against their dad, that their mom intervening was the only reason Sammy had been allowed to come. Novak doesn't need to know his family drama.

"I'm glad to hear it. I wish I was closer to my brothers. Gabriel was in town last month and didn't even bother to call me until he was already back in New York."

"Yeah, family's weird," Dean says, but he's already distracted by the idea that Novak watches his show. Novak continues talking as though he hadn't just revealed this fact to Dean, completely oblivious to the turmoil happening in Dean's head.

As the day progresses, Dean works his way around the idea of his boss watching his cam, picking up signs of it as he goes until the evidence has grown to a mountain that cannot be ignored. Novak's reaction when he first saw Dean, the fierce way he insisted that Dean maintain his self-worth. The unconscious looks of lust he gives Dean, particularly the morning after one of Dean's shows. They never make Dean uncomfortable, not when Dean has had to fight his own similar look on more than one occasion, but he has no idea how he could have missed the pattern of them.

The problem now is that Dean has no way of flat-out asking Novak if he watches Dean jack off on camera without ruining his internship. Ideally he would ask, Novak would confirm, and they would fuck in the office the way they both obviously want to. But Dean could be wrong, and if he is, there is no doubt that he would be fired on the spot, even as nice as Novak has been to him. If he were lucky, very, very lucky, Novak wouldn’t contact the university about the misstep, but past experience says that luck is never on his side.

So he cannot ask, but he is almost certain he’s right, and he can't go to work every day without confirming his theory. There has to be a way without out-right asking.

An idea comes to him on the walk home from the bus stop, and he immediately detours to the nearest corner grocer, hoping against hope that they have the thing he needs. He pulls up recipes on his phone on the way, looking for something that will fit his plan. He grins when he finds it, something easy to make that doesn’t require any cooking skills.

He’s grinning by the time he gets home from the store, sending out a tweet to let his followers know about the impromptu show as he puts away his purchases. All but one. He’s humming to himself as he begins to set up the equipment for his cam. He can say one thing for camming, it forces him to keep his tiny studio clean.

When he opens up the chatroom, he’s probably a little more disheveled than normal, but he doesn’t care. He’s grinning as the viewer number jumps. “Hey all, sorry for the late notice. I got an idea when I was at the grocery store today, and I couldn’t wait to share it with you.”

Still grinning, he picks up the thick cucumber he’d bought at the store and holds it up to the camera. “I haven’t tried one of these before. How much do you think I can take?”

/

Novak gives him the same heated look Dean has become accustomed to the mornings after cam shows, even if he hadn’t realized that was what was happening. “Good morning, Mr. Novak,” he says, smiling at his boss.

Novak returns the smile with a nod. “Good morning, Dean. Did you have a nice night?”

“I had an excellent night. I even had time to make us lunch today.” He had already put the container in the fridge in the staff lounge, not wanting to give away the surprise. He knows he is going to be anticipating Novak’s reaction all morning, but he also thinks it is going to be worth it.

“Oh? You didn’t have to do that.”

“I know, but you’ve really taught me a lot here, and I just wanted to do something to thank you.”

Novak smiles a warm, appreciative smile that settles in Dean’s belly in a very different way than his other looks have. “Thank you. I don’t know that anyone has made me a home-made lunch since I was a child. I can’t wait to find out what it is.”

Dean can’t wait to see his face when he sees it, either.

/

An agonizing morning later, Dean knocks on Mr. Novak’s office door at exactly 12:00pm with the plastic container of their lunch, two plates, and utensils. Mr. Novak calls out his consent for Dean to enter and gives him a once-over that Dean doubts is conscious from his seat behind the ultra-modern glass-topped desk that Dean still thinks is the most ridiculous thing he’s ever seen. “Is it lunchtime already?” Mr. Novak asks.

“Yep.” Dean approaches the desk, excited, but also more nervous than he’s been in a while. What if he’s wrong? What if he’s right, but Novak didn’t want Dean to know or acknowledge that he knew?

“So what did you make us? I must confess, I’ve been anticipating finding out all morning. It has made the morning go agonizingly slowly.”

Dean sets the plates and utensils down on the desk and walks around to Novak’s side as he opens the lid to show Novak what he brought. “I made us a cucumber Caprese salad. I had a couple cucumbers hanging around my place, and you’re always complaining you want to eat healthier, so I thought…” He trails off at the intense look of lust Novak is giving him. It is both scarier and a thousand times hotter than any look Novak has given him to date.

Dean smirks, vindicated that he had been right and a little turned on knowing Cas has been watching him and probably jacking off to him on the regular. He settles his ass against the edge of Cas' desk, standing a little closer to Cas' chair than is strictly professional. "Do you like cucumbers, sir? I wasn't sure if you would," he says, still keeping his innocent facade. At this point, he’s positive he's right about Cas, but just in case this is just another one of Cas' weird quirks, he wants to keep his bases covered. Besides, Cas looks like he might get off on Dean playing up the innocent act.

“You know,” Novak says, not blinking as he pins Dean with his eyes.

“I know what?” Dean asks, batting his eyelashes in the most coquettish way he can manage.

“Lock the door, please.” It isn’t a request. Dean raises an eyebrow, but does as asked.

“Why’d you want the door locked, Mr. Novak?” he asks as he walks back to the desk, still pretending innocence.

Novak slumps against the back of his chair, the most relaxed Dean has ever seen him sitting down. He hasn’t taken his eyes off Dean since the salad was revealed. “You can stop pretending you don’t know that I watch your internet shows. What gave me away?”

Dean circles the desk again, figuring formality is probably out the window at this point, and pushes the keyboard and other office supplies out of the way to make room to sit on it between Cas’ legs, pulling the container of salad onto his lap and beginning to pick at it with one of the forks he’d brought. Now that the cat is out of the bag, it’s a relief to be able to lay it all out on the table. “I never told you about Sammy coming to visit, but I did tell my viewers. After realizing that, it didn’t take long to figure out that you look at me like you want to throw me on the desk and fuck me the morning after every one of my cam shows.” Dean pops a ball of mozzarella in his mouth, smirking around the fork at Novak.

Novak looks disconcerted for a moment, stiffening and fumbling with his tie. “I hadn’t realized I looked at you that way. I apologize.”

“No need. I like it when you look at me like that.” Dean wedges the toe of his shoe under the lip of Novak’s chair and wheels him closer until his knees are settled between Dean’s open ones. “Tell me if this is out of line,” he says as he leans into Novak’s space and holds a fork full of cucumber to Novak’s mouth.

Novak eyes the cucumber with unbridled lust. “Is this the cucumber you used last night?”

“Yep,” Dean confirms with a little pop to the P. “I cleaned it with bleach and peeled it, first, so it should be fine to eat.”

He pauses before opening his mouth for the fork and gently pulling the bite off the tines with his teeth. “I shouldn’t find it so appealing to eat something that was inside you,” he says, pink creeping onto his cheeks.

Dean grins. “You saying you like the idea of maybe tasting my ass on your lunch, sir?”

Novak reaches up to smooth his hands over Dean’s hips, taking a handful of the tops of Dean’s rounded ass and squeezing. “If you’ll let me, I’d like your ass to be my lunch.”

“Fuck yeah,” Dean mutters as he goes in for a kiss. He quickly finds himself on the receiving end of the most dominant kiss of his life. Novak stands up between his legs and grabs a chunk of his hair, pulling his head back and taking over Dean’s mouth with his tongue. Dean moans into the kiss, dropping the salad container to the side and wrapping his hands around Novak’s waist for dear life. The way Novak inserts himself into Dean’s space without apology or asking permission makes Dean’s toes curl in his shoes.

When Novak pulls back to look at him, Dean knows he must look like a wreck, hair mussed, eyes lust-blown. His cock is hard and pressing against the matching hardness he can feel in Novak’s pants. “That is why I wanted you to shut the door.”

Dean manages to pull enough of his sense back together to smirk up at his boss. “And what if I’d said no?”

“Then, you could have reported me to HR and had me fired. Are you planning to do that?”

“Not unless you don’t fuck me on this stupid desk before lunch is over.”

Novak frowns, the lust receding for just a moment. “You think my desk is stupid?”

“It’s a piece of glass on two metal saw horses. Yes, it’s stupid. And I really want you to fuck me on it.”

Novak pushes his hair back from his face, looking at him less with lust and more with a new interest. He drags a finger over Dean’s lips, dragging the bottom one down just a bit. “Do you?”

Dean tries to be patient, but he’s been thinking about this too long and now that he’s had a taste, he wants all of it. “Mr. Novak?”

“I would like you to call me Castiel when we are alone. Or sir. I like it when you call me sir. But no pet names, no baby or honey or sweetheart.”

Dean tugs at Castiel’s tie, grinning mischievously. “Can I call you daddy?”

The lust is back. “Only when I’m fucking you.” He leans down for another filthy kiss set to ruin Dean for anyone else but him. Dean wraps his legs around Cas’ waist and uses the extra leverage to arch himself up closer to Cas, rubbing their erections together, a deep groan rumbling in Cas’ chest at the contact.

Cas pulls away before Dean is ready and is sitting back in his chair before Dean can blink himself back to reality. “We’re getting ahead of ourselves. Lunch first, I think. You went to all that trouble to make us such a delicious meal. It would be a shame to let it go bad, don’t you think?”

“Huh?” Dean asks, trying to shake himself from the fuzzy, floating feeling he’d gotten in Cas’ arms.

“Lunch. We are going to eat it before it gets warm and goes off. And then I am going to eat the delicious dessert you bought me.”

“Dessert? I didn’t bring…”

“You are the dessert,” Cas explains with a pointed look.

“Oh.” Dean feels his cheeks warm, which is the most ridiculous thing considering he was just talking about how much he wants Cas to do just that. He clears his throat and sits up, brushing the fuzzy haze from his brain as he picks the container back up. “But lunch first?”

“Lunch first.”

“Fine,” Dean grumbles, picking up the fork again and shoving a slice of tomato into his mouth. Cas raises an eyebrow at him before looking pointedly at the salad, and he realizes Cas means for Dean to feed him. Dean grins. He can get behind that. He stabs a cucumber and mozzarella ball onto the fork and holds it out for Cas to eat.

They soon have half the container empty and Dean is so far on the edge of the desk he’s practically in Cas’ lap, Cas nestled between his legs, hands caressing up and down Dean’s thighs. “So, how long have you been watching my cam?” Dean asks.

“I found you your second week and couldn’t stop watching you.”

“Yeah? No wonder you looked so surprised my first day.”

“I thought I was still asleep and you were a figment of my dreams.”

Dean gives him a wicked smile. “Dream about me a lot, do you?”

“Frequently.” Cas accepts the bite Dean holds up to his mouth.

Dean chews on a bite of his own, thinking this over. “So, if you’ve been watching me for so long, what’s your username? Would I recognize it?”

It’s the first time Cas looks away from him, down to his lap, a blush creeping up his cheeks. “You refer to me as Bee-man.”

Dean drops the fork. “What?” he asks, unable to stop himself from gaping at Cas.

“I probably should have told you when you first started here, given our… history.”

“Are you fucking kidding me?” Dean can’t stop himself. He is completely floored by this revelation.

“I’m sorry,” Cas says, still not looking at Dean. He picks the fork up and sets it on the edge of the desk, still without eye contact. Dean is having none of that. He slides off the edge of the desk and right into Cas’ lap, not caring how uncomfortable it is straddling the arms of the chair as he pulls Cas into a kiss. Cas makes a choked, surprised sound, his hands cautiously coming to hold onto Dean’s waist. Dean ignores his hesitation, barreling ahead without care. He buries his hands in Cas’ hair, messing up the already unruly strands as he kisses Cas with all the enthusiasm of an over-eager porn newbie.

When he finally pulls away to breathe, Cas is looking at him like he can’t believe Dean is real. “Do you have any idea how fucking happy I am that you’re Bee-man? You’ve made me come more times than I can count.”

Cas smiles this dorky little smile that makes Dean want to ride him, hard. “I can safely say the same.”

Dean snorts, leaning down to kiss him again before climbing back onto the desk, feet propped up on the arms of Cas’ chair. “You bought me that dildo you made me come un-touched on, you know.”

“The purple one?”

“Mhmm, all those private chats. You really wanted me to yourself, didn’t you?” he teases.

“I did. This is… much better.” Cas reaches for him, pulling Dean closer and spreading his hands over Dean’s hips. His eyes darken as he thumbs the top of his hip joints. “In fact… get up and turn around. And lose the pants.” Cas wheels himself back far enough to give Dean room to hop down from the desk. Dean makes quick work of his shoes and pants, leaving the pink satin panties he’d put on specifically anticipating this scenario. Cas groans behind him as a hand caresses his ass cheek over the satin.

“You like?” Dean asks over his shoulder, leaning over the desk to present his ass for Cas’ examination.

Cas smooths both hands up over his hips, thumbs rubbing over the fabric, his face taking on a look of reverence. “Do you wear women’s underwear every day?”

“No, they’re just for you. I thought you might like them.”

“I do. Very much.” He fingers the edges of the panties, sliding his fingertips under the elastic and slowly pulling one side over, exposing Dean’s entrance. He thumbs at it, smiling at the shiver that goes through Dean. Dean’s the only person who’s touched his hole in months, and it feels even more amazing knowing that those are Cas’ fingers touching him now. Cas looks up at Dean as if asking permission, and Dean nods, game for whatever Cas wants to do to him. Cas lowers his head, and Dean’s moaning even before he feels the hot tongue flatten out against his rim. Cas spends a few minutes taking long, drawn-out licks of him, his hot tongue pressing hard into every curvature of Dean’s crack. Every exaggerated lick sends a spark of frustratingly mild pleasure through Dean. He clings to the edge of the glass desk top, trying to keep his moans quiet because he didn’t lock the outer door and has no idea how thin the walls of the office are.

Cas pulls his tongue away long enough to say, “Make as much noise as you want. No one is going to hear you.”

“But what if someone walks into my office looking for you?”

Cas growls and stands, leaving Dean propped up on the desk to watch as he stomps to the door, unlocks and pulls it open, and crosses Dean’s part of the office to lock the outer door. He shuts the inner door behind him, giving Dean a dark look that turns his insides to molten lava. “I repeat, make as much noise as you want,” he orders as he rounds the desk again and settles back into his chair. He buries his tongue as deep into Dean’s ass as he can the next instant and Dean cries out in pleasure, holding tight to the desk again.

“Fuck, Cas…” he murmurs into his bicep, hiding the warmth of his cheeks with his arm, a little embarrassed by how flushed he is. He pushes his hips back into Cas’ mouth as Cas spreads his cheeks wider with his hands, teasing a finger in next to his tongue. Dean can already feel himself leaking pre-cum onto the floor, so hard it almost hurts. He reaches down to stroke himself and try to relieve the pressure, but Cas smacks his hand away.

“No touching,” he commands before burying his face back in Dean’s ass. His thumb begins rubbing at Dean’s perineum, soft back and forth that only helps to drive Dean up the wall with need.

“You’re gonna kill me. Come on…”

A sharp slap across his ass cheek is his answer. He jumps a little from the shock, but pushes his ass towards Cas again a moment later, whining a little. Cas doesn’t let up on his tongue-fucking. Soon Dean is crying out, begging to be fucked, feeling like he might unravel at any moment if Cas doesn’t get his cock in him.

“Come on, Cas, don’t you want to fuck me?” he rasps out, rocking his hips back. It earns him another slap of his ass, but it also gets him what he wants. Cas pulls away and turns around to start rifling through a cabinet set under the windows that make up the back wall of the office. He comes back with a condom, and Dean is happy to see he had already gotten his cock out while he had his tongue up Dean’s ass. Dean straightens up and turns around to stroke at Cas’ thick shaft while Cas gets the condom open. “You gonna fuck me with this big cock, daddy?” he whispers, grinning at the heated look it gets him.

Cas pulls him in with his free hand and kisses him dirty. Dean grins against the kiss, happy to be lifted onto the desk, happy to have Cas so close between his legs. He takes the condom from Cas without pulling away from the kiss and rolls it down Cas’ cock, stroking it to test the condom lubrication. Cas pushes him backwards to lie across the desk, the keyboard momentarily acting as a pillow before Dean grows irritated with it and shoves it off the edge of the desk, mindless for the sound of it hitting the carpeted floor. Cas pushes his knees up to his chest and leans over him to keep kissing him as he rubs the head of his cock over Dean’s rim, teasing him. Dean whines, too overstimulated and ready to get to the main event.

He doesn’t have to wait long. Cas groans as he sinks into Dean almost as deep as the cucumber of the night before. Dean drops his head back with a moan, holding onto the backs of his knees as Cas bottoms out. He reaches behind him to grab the edge of the desk to anchor himself as Cas starts to move, slowly at first, but increasing his pace as Dean’s moans grow louder. Cas leans over him for a kiss, grinding his dick in against Dean’s prostate over and over again. Between the extended rimming and the brutal attack on his prostate, Dean loses the tentative thread of composure holding his orgasm back. He shoots hot cum all over both of their pressed white dress shirts.

Cas kisses him through his orgasm and doesn’t stop thrusting into him, even when Dean whimpers from the overstimulation. Dean can do nothing but lay back and take it as Cas pounds into him. The desk skids across the carpet, shifting dangerously, and Dean has a moment of worry that Cas might push it—and him—right off the shiny chrome base. “Fuck, Cas… don’t break the desk,” he warns, reaching up to wrap his arms around Cas’ neck to get closer to him. Cas shuts him up with another long kiss. He has his arms around Dean, holding onto his shoulders as he pounds into him.

He lasts longer than Dean would have expected, but the signs of impending crisis creep up over his face after a while, and Dean grins at him. “You gonna come for me, daddy? You gonna give me that hot cum of yours?” Dean normally doesn’t talk this much during sex, but he can’t seem to shut his mouth with Cas fucking him like this. Cas groans, burying his face in Dean’s shoulder as his hips jerk out of rhythm. He clings hard enough that Dean thinks he might have some tender skin later, but he can’t bring himself to mind.

When Cas pulls away from Dean’s shoulder, he’s flushed and sleepy-looking. Dean kisses him, tightening his arms around Cas’ neck as he does. Cas lets him control the kiss, returning it with lazy, slow movements. He picks Dean up and helps Dean get situated on his lap as he collapses back into his chair. Dean trails kisses all over his face, unable to stop smiling despite the stains on his dress shirt and the squished feeling of his loose, sloppy-feeling hole.

When they finally pull away, Dean pushes Cas’ sweaty hair out of his face. “So that was fucking awesome,” he says.

Cas grunts agreement, rubbing one hand up and down Dean’s back. “Understatement.”

Dean looks behind him to check the time on the computer, blushing when he sees that it’s well past one. “You missed the board meeting.”

“I didn’t need to go anyway. If anyone asks, I’ll just tell them I was busy fucking my intern into my desk. I’m sure they’ll understand.”

Dean snorts. “Yeah, that’ll work.” When he turns back around, Cas is watching him.

“I enjoyed this quite a lot. Would it be inappropriate to ask if it can… continue?”

Dean pretends to think for a minute, but that’s only so he doesn’t seem over-eager. “Yeah, we can definitely keep this going. Obviously we’re not telling anyone at the office?”

“Of course not, though I would be surprised if Meg doesn’t figure it out as soon as she sees you in my shirt.”

“You’re shirt?” Dean asks, confused. Cas rubs at the obvious cum stain on his dress shirt and he remembers. “Right, yeah. You uh, you got a couple spares?”

“There’s a small hanging closet in the bathroom. I’m not always conscious enough in the morning to check that my shirt has been ironed before coming in to work.”

Dean nods, fiddling with Cas’ tie. “Should we get back to work, then?”

Cas makes a pained face. “I suppose.” But when Dean tries to get up, Cas pulls him back. “Just a few more minutes, perhaps.” He pulls Dean back in for another kiss. A few more minutes turns into half the afternoon, but thankfully no one notices.

/

.Epilogue

Dean crawls up on the bed, grinning and waving at the camera. “Hey all, I know it’s been a few days since I logged on. I’ve uh… had some life changes, if you couldn’t tell from the scenery change. As most of you know, I met Bee-man through some unforeseen coincidences, and we’ve been seeing each other for about six months now.” Dean looks up over the webcam at Cas, seated in a chair in the corner of the bedroom wearing just his robe. Cas smiles back at him, resting his temple on his hand, propped up on the arm of the chair. Dean grins and looks back at the camera. He checks the chat box and nods. “Yeah, I know, he’s a pretty lucky bastard, right?” he says in response to **hotcajun1872**.

“Anyway, my lease was up last month, and since things are going so well between Bee-man and me, he asked me to move in with him.” Dean grins over at Cas again, unable to help how goofy the smile probably looks. “So I did,” he indicates the room behind him, the tall leather headboard to his side and the huge gold-framed mirror at his back. Cas’ bare legs and feet are just visible in the mirror, “hence the location change. If you follow me on Snapchat or Instagram, you probably saw my moving process.” He reads a few lines of the chat, bobbing his head at their responses. “I’m Impala67 on Snapchat and Instagram, same as here.”

“No, Bee-man isn’t going to be joining me over here for now, but if you look close in the mirror, you can see his legs in the corner over there.” Dean points to the mirror. “He’s going to be here for most of my videos from now on. I hope no one minds. There will be benefits, I promise.”

 **Morningstar666** expresses worry at Dean being in a relationship. “No need to worry, I’m definitely not quitting the cam business. Bee-man watches my cams too, remember? He wants me to keep camming as much as I want to keep at it. Bee-man’s even going to be in some of them. Not his face, ‘cause he’s got a big fancy corporate job he doesn’t want to fuck up, but the rest of him. You’ve all said you wanted me to try having another person on my cam with me, right? You wanted to watch me get fucked by another dude?”

He gets a few negatives, but an overwhelming majority of his responses are positive. “I do have to let you know this is probably going to be my last cam for a couple of weeks, maybe a month.” There is a flurry of protests following that confession. Dean holds his hands up to try to calm them all. “Don’t worry, I’ll be back. Bee-man’s taking me to Greece on vacation.” Dean grins over at Cas, still disbelieving himself. He took road trips with his family when he was a kid, but he hasn’t been able to afford anything approaching a vacation since his dad kicked him out at eighteen. And he’s never left the country before. Two weeks touring the Greek islands is going to be amazing. And Cas already promised to fuck him on the beach of every island they visit. “We’re not bringing a computer, but we will probably be filming a couple videos on our phones and uploading them. I’ll announce when I post them, with links.”

He fields more questions, un-surprised by how concerned his viewers are that his life is changing. A lot of these people have been watching Dean for at least a year, some for as long as three. Hell, Cas had been watching him since his second week, video grainy on the shitty laptop he’d bought at a pawn shop for $50, Dean three months out from his eighteenth birthday and all bravado, but no clue what he was doing. In the four years since, Dean has grown as a person, as well as a performer, but this is the first major change in his life his viewers have experienced, and he can understand their worry.

Ten minutes later, he’s talked them all down off the ledge, and starts seeing ‘Are you gonna get naked anytime soon?’ questions, mostly from his free viewers, but he doesn’t mind. “Impatient, aren’t you? No need to rush, buddy, we’re gonna be here for a while.” He winks over at Cas, still watching him quietly in the corner. Dean can see he’s finally started in on the whiskey Dean left for him.

Dean looks back at the camera and smiles, crawling up on his knees on the mattress and knee-walking backwards to get fully in frame. He pulls his shirt over his head without preamble, starting to get as impatient to get this show going as the viewers are. He runs his hands up and down his chest, tweaking a nipple every once in a while. He sees **Morningstar666** question the new ink on his chest and grins, rubbing his fingers over the still-sensitive skin above his heart. “I did get a new tattoo, yeah. My brother came to visit again to meet Bee-man and celebrate his birthday. He just turned eighteen, and we sort of talked each other into getting matching tattoos. A bonding thing, I guess? You like?”

Dean leans up closer to the camera to let them get a better view of it. He laughs at Morningstar’s response. “It isn’t demonic. It’s a protection symbol. It’s supposed to keep all the demons and the baddies at bay.” He leans back on his heels again, reaching down to start in on his pants. He’s wearing a pair of red lace panties underneath, with a lot of straps that meet under a bow just below the dimples of his ass cheeks, but not a lot of actual fabric. They don’t function as underwear in any practical way, but they make him feel slinky and sort of Jessica-Rabbit-sexy, and the way Cas looks at him when he wears them is the best feeling in the world. Cas is looking at him that way now, he can see through the mirror, his own angle making it easy to see Cas’ eyes glued to his ass. He smirks to himself and pushes his jeans off, dropping onto his side to pull them off his legs. He keeps his back to the camera for a minute, stretching the elastic straps and adjusting them to the perfect angle to frame his bubble butt.

He turns around at a flurry of pings, pleased to see half a dozen requests for private chats. “In a little bit, I promise. I’m glad you like the new panties. Bee-man got them for me.” He wiggles his ass a little and playfully slaps one cheek. He turns around, showing off the low dip of the front of them, just another thick V of lace connected with another series of straps just at the edge of his pubic hair with another bow. His erection is tucked into one side, but the head is already peeking out. He pulls it out of the lace and strokes it through one of the gaps between the straps.

He grins at the compliments that follow, as well as the instructions to do things like fuck his fist or pull the panties aside and show off his ass. He strokes himself for a little while longer, getting himself to full hardness, occasionally glancing over at Cas in the corner and the obvious tent in his robe. He bites his lip, scooping a thumb over his head. “Are you guys ready for something a little dirtier?” he asks, voice dropping an octave from arousal.

He watches the chat, smiling. “Yeah? I can do that. Not right now, though. For all of you who have been wanting to see me suck a real live dick, you’re about to get your wish. Bear with me a minute while I get the camera situated. If you have any requests, let me know now. I’m going to go over to Bee-man, so I won’t be able to see the chat for a while.”

Dean zooms the camera into the mirror, adjusting it so that Cas is visible from his waist down. He’s glad Cas bought him a better resolution camera for his birthday, otherwise the picture would have been terrible. “Okay, we’re gonna go into the premium room now. Remember, you are welcome to subscribe to my channel at any time or pay for one-time access. Since I’ll be across the room, I can’t respond to private chat requests while I’m sucking Bee-man off, but we’ll talk about it after, okay?” He checks the chat for any final comments before switching to a premium room. One final check that everything is running smoothly and he gets up and walks over to the chair in the corner.

He leans over Cas long enough to kiss him before dropping to his knees at Cas’ feet and gliding his hands up Cas’ legs. Cas smiles, eyes glued to Dean’s face as Dean parts the folds of the robe, uncovering Cas’ half-hard cock. “Ready for you debut?” he asks softly.

Cas reaches down and combs finger through his hair, pulling him up for another lingering kiss before letting him get to it. Dean grins, taking ahold of Cas and giving kitten licks to the head, fluttering his tongue over the tip. Cas drops his head against the back of the chair and groans, his fingers gripping the chair arms. Dean wraps his lips around the head and sucks, slowly at first, just the tip, but gradually taking more and more in until he has most of the shaft in his mouth and Cas’ head is bumping against his throat.

He’s fully hard now, and Dean takes advantage, letting go with his hands and bobbing his head up and down the stiff shaft. He takes hold of Cas’ ankles to keep his hands occupied as Cas starts to thrust up into his mouth. One of Cas’ hands wraps around the back of his head, holding him in place as Cas begins slowly fucking his mouth, long strokes that are deep enough to choke Dean, but gentle enough not to. Dean moans around his mouthful, feeling himself start to leak pre-cum and shifting his hips to try to get a little friction. It doesn’t work.

Cas pulls him off, stroking Dean’s lips with his thumb as he lifts Dean’s head up for a heated kiss. Dean is a little fuzzy when he pulls away, a feeling he’s gotten used to when Cas kisses him that way. He tries to go back to the blowjob, but Cas shakes his head. “You keep that up, you’re going to make me come before I get inside you.”

Dean whines at the suggestion, crawling up into Cas’ lap to get the process going. Cas chuckles and kisses him, squeezing his ass under the panties, teasing just at the edges of his crack without actually touching his hole. Dean whines again, squirming in Cas’ lap, not above begging to get what he wants. “Daddy, please…” he whispers against Cas’ lips.

“I think you want your viewers to watch me open you up, don’t you?”

Dean glances back at the camera, having temporarily forgotten about the show. He blushes and nods, biting his lip in embarrassment for the slip-up. Cas caresses his cheek, fingers smoothing over the flushed skin.

“You are so gorgeous when you blush,” he murmurs before leaning in for another kiss. Dean moans into his mouth, wrapping his arms around Cas’ shoulders as Cas gets a good grip on his hips and stands up. Dean wraps his legs around Cas’ waist, gripping tight to help Cas with his weight. They make it over to the bed and Cas drops him onto it, no doubt keeping his face out of camera range. Dean spreads out on the mattress as Cas adjusts the camera for him again, making sure to get most of his body in frame, his bowed legs the only part of him out of view. Cas kneels on top of the bed, letting his robe drop over the edge. He’s just out of range of the camera, his hands pulling Dean’s hips closer the only thing visible.

Dean sucks a finger into his mouth, waiting for whatever Cas has planned. He looks at the screen to see they’ve gained a couple dozen new subscribers, many of whom Dean doesn’t recognize. Dean grins at the camera, moving his wetted finger to his nipple and pinching it, arching up at the pleasure of it. Cas tugs at the panties, sliding them off of Dean’s hips and up his legs until they join the robe on the floor. Dean lets his legs drop to either side of Cas’ knees, giving him full access. Cas takes every advantage.

Dean watches through his spread legs as Cas trails lube-slick fingers up his thighs to rub them around his pucker, using his dry hand to push one of Dean’s leg up and out of the way of the camera. Dean closes his eyes as Cas’ first finger enters him, pushing in nice and slow. Dean knows better than to try and jack himself at the same time, so he turns his head to look at the chat box to distract himself from his serious need to touch himself. He smiles at the comments.

“You like the camera work? It helps to have a guy who’d normally be on the other side of the screen working with it, huh?” Cas adds a second finger and digs them both deep enough to get to his prostate, making him cry out and rock his hips towards them, trying for more.

He looks at the chat again and chuckles. “Yeah, he hit the spot alright. Mmm, fuck….” He murmurs as Cas does it again. He looks up at Cas, worrying his bottom lip between his teeth as he arches his hips closer, hoping to entice Cas to fuck him already. Cas firmly pushes his leg onto the bed, keeping him in place as he keeps fingering him.

“Move again, and I’m not going to let you come on my cock,” Cas growls, making Dean whimper and arch higher.

“Please, daddy…”

“Patience.” Cas drops his eyes back to his fingers dipping in and out of Dean’s ass, and Dean can’t help but cry out as his prostate is mercilessly rubbed. 

It feels like an eternity before Cas pulls his fingers out, but Dean’s a little too far in bliss land to notice until Cas is moving him again, pushing both his knees up to his chest. Dean tries to hold his knees himself, but Cas gives him a sharp look. “Keep your hands above your head,” he says. Dean quickly complies. Cas strokes a thumb over his cheek, smiling fondly. “Good boy. Do not move until I give you permission.”

“Yes, sir,” Dean murmurs, focused on watching Cas roll the condom onto his cock and slick it up with lube. He leans over Dean, using one hand to guide himself to Dean’s hole and tease him with the head a few times. Dean can’t help but squirm a little, trying to get more friction between them. Cas smirks down at Dean, balancing himself with his other hand holding the back of Dean’s thigh as he begins to sink in. “Fuck…” Dean moans, rolling his head back. They’ve been fucking for a solid six months now, and it still feels amazing every time Cas slides in for the first time.

Cas begins to thrust, putting all his weight on his hand holding Dean’s thigh to his chest. The angle lets him hit directly into Dean’s prostate with every thrust. Dean can’t help the tiny moans that fall from his mouth at every one. He stretches his arms as far behind his head as he can, arching his back and rolling his hips into Cas’ as much as Cas’ hold on him allows.

By the time his orgasm rolls on in, he’s a complete mess, tears leaking from the corners of his eyes, fists white-knuckling the pillow that somehow ended up under his head—Cas’ doing, probably. His body explodes in pleasure, cum bursting form his cock like a geyser. He shakes with the strength of it, jerking with each new shock. Cas groans above him, eyes shut tight and his hands gripping Dean hard enough to whiten his skin as he hits his own peak. Dean recovers from his just soon enough to catch the blissed-out look on Cas’ face.

Dean can’t keep the goofy smile off his face. He glances at the computer and is amazed to see the tips tally at well over two grand. “Holy shit, you guys. Thank you. I take it you liked that as much as we did?” he asks.

A flurry of positive responses run up the chat screen. There are also about a hundred requests for private chats, but Dean is too sleepy to accept any of them. Cas collapses on top of him, the back of his head facing the camera, and Dean takes a few minutes to pet his hair and cuddle him close as his viewers praise their ‘performance’. “Thank you, guys. I really appreciate the compliments. I’m glad you’re cool with me adding Bee-man to the show.” Cas shuffles closer to him and presses lazy kisses to his neck. Dean turns his head to kiss him, cupping his cheek to make sure his face stays hidden.

Eventually, he shifts Cas off and behind him and sits up. The cum is dried on his chest. He picks at it as he begins typing out apology messages to all the private room requests. “Sorry everyone, but I’m just too tired. Bee-man fucked me up good.” He grins at them all. “Forgive me?” He gets a dozen positive replies. “Thanks. So, like I said at the beginning of the show, this is probably going to be my last show for three weeks, maybe a month. Bee-man and I are going on vacation for two weeks to celebrate the end of my semester and moving in together.”

Dean pauses when Cas rolls into him, his head just out of frame of the camera, and wraps an arm around Dean’s waist. “I also just enjoy spoiling you,” he tells Dean, his voice impossibly deep post-orgasm.

Dean smirks. “That, too. Anyway, thank you all for being so supportive of me. Bee-man and I will probably film some videos of us fucking on the beach during our vacation, so if you want to catch any of them, make sure to follow me on Twitter or Instagram. I’ll also be snapping some of the awesome stuff we see, so if you’re interested, follow me on Snapchat, too. I’m Impala67 everywhere. Thank you all again. I hope you have an awesome rest of your week. Good night.” Dean blows the camera a kiss and sees Cas waving the hand he had around Dean’s waist before he closes out the cam and logs off.

As he settles under the covers with Cas later, he can’t stop smiling. “Are you happy?” he asks.

“Blissfully. You?”

“Yeah…”

Cas turns to him, cupping his face and kissing him with a tenderness he’s never felt before. When they pull away, Dean is smiling as he buries his face in Cas’ shoulder. He falls asleep to the soothing feeling of Cas combing fingers through his hair.

**Author's Note:**

> If you want writing updates from me, you can follow me on Twitter [@RonsPigwidgeon](https://twitter.com/RonsPigwidgeon) or Tumblr at [MsCaptainWinchester](https://mscaptainwinchester.tumblr.com/).


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